3-Methylbenzoyl chloride

clear colorless to light brown liquid

In a 1000 ml reaction flask equipped with a thermometer, a stirrer, a condenser, and an exhaust gas absorption device, 540.56 g of m-toluic acid, 573.0 g of thionyl chloride and 1.0 g of N, N-dimethylformamide were charged and heated to 90 ° C, the reaction was stirred 3h, the reaction was completely transparent, excess pressure to remove excess thionyl chloride, m-methyl benzoyl chloride 610.0g, purity 98.2percent, yield 99.3percent om-methyl benzoyl chloride continuous production process is as follows: (1) m-methylbenzoic acid 1360kg, 1453kg thionylchloride and 2720kg xylene were added to the reactor. Then, addition of 2.04kg tetrabutyl ammonium hydrogen sulfate. At 45 deg.C reaction 4h, until no gas evolution. Continue to hold temperature for 0.5 hours, to obtain a reaction solution;(2) The reaction mixture was added tothe distillation column, flow into the tower 4.7kg / min, distillation tower bottoms heated by steam, Temperature controlled at 105 , overhead light component recovery flow 4.2kg / min, light component after condensed by the condenser returned to the reaction vessel; (3) the distillation tower reactor m-methylbenzoyl chloride crude product was added to the thin film evaporator, feed rate of 3.9kg / min, adjust the degree of vacuum to 630mmHg, vacuum distillation at 127 deg.C, to give 1516.5 kg-methyl chloride in a yield of 98.2percent, after testing, chromatography between methyl chloride content of 99.4percent.(1) Add 330 g of m-toluic acid to the reaction vessel, add 360 g of thionyl chloride and 5 g of DMF, and stir for 2 h. When there is no obvious gas in the reaction vessel, the temperature is raised to 90 ± 5 ° C. Incubated for 2 h to complete the reaction, and then distilled at 120 ° C excess excess thionyl chloride. M-methyl benzoyl chloride yield of 98.9percent;The catalyst dissolved in fresh m-xylene added to the oxidation reactor isN-hydroxyphthalimide, Cobalt naphthenate, Metal phthalocyanine having the structure of the general formula (IV) (R1=H, R2=H, M=Co) and metal porphyrin having the structure of the general formula (III) (R1=R2=R3=H, M1=M2=Mn )mixture, The total concentration is 800ppm and the reaction temperature is 135 °C.The reaction pressure is 0.5 MPa, and the oxygen-containing gas is pure oxygen. The operation procedure is the same as in the first embodiment.The difference is that the conversion of meta-xylene is controlled at 36percent.The content of intermediate methyl benzyl alcohol in the initial steaming tower was controlled to be 0.05percent.The mass percentage of each component obtained by HPLC analysis in the reaction solution is shown in Table 1.The quality of the obtained steaming tower bottom liquid, The contents of the methyl benzoic acid in the mixture of the composition and the initial distillation column are shown in Table 2.The above-mentioned preliminary steaming tower bottom liquid is subjected to rectification, At the top of the column, 376.6 g of m-methylbenzoic acid product with a purity of 99.0percent was obtained.In the column, 1718.8 g of a high-boiling tower liquid having an m-methylbenzoic acid content of 86.5 wtpercent was obtained.Taking thionyl chloride as the acid chloride reagent, The high boiling column liquid is subjected to an acid chlorination reaction, Obtaining an acid chloride reaction solution whose main components are m-methylbenzoyl chloride and isophthaloyl chloride, The reaction end point is the content of m-methylbenzoic acid <0.5 wtpercent.The obtained acid chloride reaction solution is subjected to rectification separation, At the top of the column, 1655.4 g of m-methylbenzoyl chloride and 99.0percent of isophthalic acid were obtained in this order.The acid chloride was 277.9 g. Calculated based on the input meta-xylene, The yield of m-methylbenzoic acid was 17.0percent, and the yield of m-methylbenzoyl chloride was 65.7percent.The yield of isophthalic acid chloride is 8.4percent.The total yield of the three was 91.1percent.The catalyst dissolved in fresh m-xylene added to the oxidation reactor is a mixture of MnO2 and Co(Ac)2·4H2O.The compound has a total concentration of 150 ppm and a reaction temperature of 156 ° C.The reaction pressure is 1.0 MPa, and the oxygen-containing gas is pure oxygen.The difference is that the conversion of meta-xylene is controlled to 38percent.The content of intermediate methyl benzyl alcohol in the initial steaming tower was controlled to be 0.05percent.The mass percentage of each component obtained by HPLC analysis in the reaction solution is shown in Table 1.The mass and composition of the obtained preliminary steaming tower bottom liquid and the content of methylbenzoic acid in the initial steaming tower overhead mixture are shown in Table 2.The above-mentioned preliminary steaming tower bottom liquid is subjected to rectification, At the top of the column, 555.2 g of m-methylbenzoic acid product with a purity of 99.0percent was obtained.The column kettle obtained 1552.3 g of a high-boiling tower liquid having an m-methylbenzoic acid content of 84.6 wtpercent.The chlorination reaction is carried out by using sulfoxide as the acyl chloride reagent, and the high boiling column liquid is subjected to an acid chlorination reaction.Obtaining an acid chloride reaction solution whose main components are m-methylbenzoyl chloride and isophthaloyl chloride, The reaction end point is the content of m-methylbenzoic acid <0.5 wtpercent.The obtained acid chloride reaction solution is subjected to rectification separation, At the top of the column, 1461.9 g of m-methylbenzoyl chloride and 99.0percent of isophthalic acid were obtained in this order.The acid chloride was 286.7 g. Calculated based on the input meta-xylene, The yield of m-methylbenzoic acid was 71.8percent, and the yield of m-methylbenzoyl chloride was 25.0percent.The yield of isophthaloyl chloride was 58.0percent, and the total yield of the three was 8.7percent.

Used in medicine, pesticides, photosensitive materials, dyes, etc.

Molecular Weight:154.59
XLogP3:3.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:154.0185425
Monoisotopic Mass:154.0185425
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes